Woolley began his career as a producer in the 1980s with films such as The Company of Wolves, Chinese Boxes and the series The Worst of Hollywood. He was previously involved in more than 50 productions. In 1993 he was awarded for he produced feature film The Crying Game with the London Critics' Circle Film Award for Best British producer and a BAFTA Award. In addition, he received an Oscar nomination for Best Picture.
Woolley is married to the film producer Elizabeth Karlsen. The couple has three daughters.